Synthetic Methodologies Of Of C-C, C-N And C-O Bonds Based On Oxidation Rection

Organic synthetic methodology has always been any organic chemistry workers to consider and research topic. This thesis is mainly based on the research of organic synthetic methodologies to constrct the carbon-carbon bond, carbon-nitrogen bond and carbon-oxygen bond, and synthesizes a series of organic compounds, such as2-alkenyl quinolines, aromatic ketones, oxazoles and imidazo[1,2-a]pyridines compounds.Firstly, we have developed a new method for the synthesis of2-vinylquinolines, via an iron-catalyzed sp3C-H functionalization and a subsequent C-N cleavage, by reacting2-methylquinolines with N,N-dimethylformamide. This method is simple and efficient, and avoids the use of organometallic compounds. A variety of2-vinylquinolines were obtained from readily available2-methylquinolines with good yields.Then, we have researched the application of metal-free catalytic oxidation systems in organic synthesis. The oxidation of active methyls to alkenyl and the oxidation of methylenes to ketones are two important organic transformations. Traditional methods for these transformations were always using stoichiometric metal oxidants or metal catalysts. And our approaches for these transformations are simple and efficient under metal conditions with oxygen as oxidant. On the other hand, oxazoles are a very useful five-membered heterocyclic compounds not only because of their varied biological activity but also they serve as structural elements for a variety of natural products. A new metal-free decarboxylative cyclization of available primary a-amino acids with2-bromoacetophenones was developed for the synthesis of polysubstituted oxazoles in the presence of iodine and tert-butyl hydroperoxide. This method is simple and efficient with mild reaction conditions and available reactants.Finally, based on the very the important biological activity of imidazo[1,2-a]pyridines and the varies application of antibiosis, anti-inflammatory, anticonvulsant, antiulcer, immunomodulatory and drug molecules, and combined with the contribution of the catalytic oxidation of our laboratory, we developed a facile method for the synthesis of imidazo[1,2-a]pyridines via an copper catalysed with the reaction2-aminopyridine and acetophenone. This approach for the synthesis of imidazo[1,2-a]pyridines is simple, efficient and has important potential applications.